EP2384733B1 - Matières dentaires antimicrobiennes - Google Patents

Matières dentaires antimicrobiennes Download PDF

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Publication number
EP2384733B1
EP2384733B1 EP10162250.4A EP10162250A EP2384733B1 EP 2384733 B1 EP2384733 B1 EP 2384733B1 EP 10162250 A EP10162250 A EP 10162250A EP 2384733 B1 EP2384733 B1 EP 2384733B1
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Prior art keywords
dental material
material according
dental
weight
formula
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EP2384733A1 (fr
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Ulrich Salz
Volker Rheinberger
Kai Rist
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Ivoclar Vivadent AG
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Ivoclar Vivadent AG
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Priority to EP10162250.4A priority Critical patent/EP2384733B1/fr
Priority to JP2011096597A priority patent/JP2011236211A/ja
Priority to US13/097,100 priority patent/US20110275675A1/en
Publication of EP2384733A1 publication Critical patent/EP2384733A1/fr
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/15—Compositions characterised by their physical properties
    • A61K6/16—Refractive index
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/15—Compositions characterised by their physical properties
    • A61K6/17—Particle size
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
    • A61K6/69—Medicaments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/70—Preparations for dentistry comprising inorganic additives
    • A61K6/71—Fillers
    • A61K6/76—Fillers comprising silicon-containing compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/70—Preparations for dentistry comprising inorganic additives
    • A61K6/71—Fillers
    • A61K6/77—Glass
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
    • A61K6/802—Preparations for artificial teeth, for filling teeth or for capping teeth comprising ceramics

Definitions

  • the present invention relates to dental materials with antimicrobial activity which are useful inter alia as restorative materials, cements, sealants, temporary restoration materials, coating materials and adhesives.
  • triclosan To suppress pathogenic intra-oral microbes, for example, for caries prevention and therapy, mouthwashes, toothpastes and gels containing an antimicrobial agent such as triclosan or chlorhexidine are used. While chlorhexidine is one of the most effective agents for controlling plaque and gingivitis, triclosan has the advantage of being non-ionic and therefore compatible with most ingredients of oral care products. Triclosan is therefore used in most commercially available products.
  • a disadvantage of these forms of application is the short exposure time. This makes a protracted, repeated application indispensable to achieve the desired therapeutic success, which in turn requires a complex aftercare. In difficult or even inaccessible populations with pathogenic germs, such as deep fissures, approximal spaces or marginal gaps, this form of therapy is unsuitable. In the bacterial colonization of marginal columns is usually only the replacement of the filling targeted.
  • antimicrobial dental materials are often used.
  • the antimicrobial effect is usually achieved by adding antimicrobial agents to the dental material.
  • the same active ingredients are used, which are also used in mouthwashes, toothpastes or gels.
  • the problem is that the physical and chemical properties of the dental material, such as its mechanical properties or the curing behavior, must not be affected by the addition of active ingredient. Also, release of the active substance must be ensured in an effective amount and for a longer, clinically relevant period of time.
  • WO 89/10736 describes a chlorhexidine-containing dental cement, which is well soluble in oral fluids and should dissolve after one to four weeks. This is intended to achieve a controlled release of the active ingredient.
  • the DE 198 13 686 A1 discloses an antimicrobial root filling material containing chlorhexidine and a iodophor.
  • the active ingredient is applied to a polymeric carrier.
  • the WO 99/20227 describes a tooth-coating material for caries prevention which contains triclosan (2,4,4'-trichloro-2'-hydroxydiphenyl ether) as antimicrobial agent.
  • curable dental restorative materials containing water-insoluble, non-cationic antibacterial substances, preferably triclosan.
  • the EP 1 566 160 A2 discloses the use of extracts of natural products with antimicrobial activity, such as grapefruit seed extract or green tea extract, for the production of dental materials.
  • the extracts are included in cyclodextrins.
  • the WO 2005/058252 discloses the use of elemental silver as an antibacterial agent for dental materials, and the EP 1 374 830 A1 describes a dental composition with antimicrobial properties containing silver-containing ceramics.
  • each of these listed active ingredients has negative properties that severely limit its use in dental materials and that call into question the clinical usefulness of these materials.
  • active substances such as triclosan inhibit radical polymerization, which impairs the mechanical properties of polymerizable dental materials and limits the amount of active substance that can be used.
  • Other active substances such as chlorhexidine, lead to pronounced blackening of teeth, tongue and fillings during prolonged oral use ( Gjermo PJ, Dent Res, Spec Iss 1989; 68: 1602-1608 ).
  • chlorhexidine leads to taste irritations and is not light-stable.
  • the EP 2 113 237 A1 discloses dental materials equipped with antiplaque agent (s) which contain as active ingredient a molecular disperse octenidine salt or dequalinium salt. These salts have anions from the group of fatty acid anions, carboxylic acid anions, alkyl and arylsulfonic acids, alkyl and aryl sulfates. These are lipophilic anions that allow mobility / migration ability of the octenidine salts in the dental materials.
  • the invention has for its object to provide dental materials that are characterized by a high antimicrobial effect and do not have the disadvantages mentioned.
  • antimicrobial active compounds of the formula (I) according to the invention can be prepared by known synthesis processes, such as, for example, in US Pat US 4,206,215 described described.
  • the active compounds of the formula (I) have a combination of properties which is advantageous for producing dental materials.
  • they are sufficiently lipophilic to be compatible with organic monomers, on the other hand they have so much water solubility that they can fully develop their antimicrobial effect. Furthermore was found not to interfere with radical polymerization.
  • the dental materials according to the invention are particularly suitable as filling materials and temporary filling materials, e.g. for prepared cavities and root canals, as underfill materials, as cements and temporary cements, for example for the cementation of indirect restorations, as sealers for pits, fissures, root canals, root, dentin and enamel surfaces, as temporary supplies, e.g. as materials for temporary crowns and bridges, as adhesives, as coating materials, etchants, and root canal sealers.
  • Preferred dental materials are:
  • Adhesives such as enamel / dentin adhesives, which require substrate conditioning with an acid prior to adhesive application (totaletch technique); self-etching enamel / dentin adhesives.
  • Temporary supplies such as temporary composite-based cements; temporary polycarboxylate / zinc oxide-based fixing cements; temporary composite-based restoratives; glass ionomer-based temporary restoratives; temporary polycarboxylate / zinc oxide based restocking materials; temporary crown and bridge materials based on composite or PMMA.
  • Filling materials such as compost filling materials, composite filling materials, composite fixing materials, bracketing elements.
  • Sealers such as fissure sealers and acrylate coating materials.
  • the dental materials of the invention contain from 0.1 to 3.0 wt .-%, preferably 0.1 to 1.5 wt .-% and particularly preferably 0.1 to 0.6 wt .-% of the active ingredient of formula (I). Unless stated otherwise, all percentages relate to the total composition of the dental materials.
  • the polymerizable dental materials are in particular dental materials that can be cured by a radical polymerization. These contain in addition to the active ingredient of formula (I) at least one polymerizable, ethylenically unsaturated monomer as a binder, an initiator for the radical polymerization and may also contain an organic and / or inorganic filler.
  • the polymerizable dental materials are particularly suitable as dental filling materials, materials for inlays or onlays, dental cements, as veneering materials for crowns and bridges, as material for artificial teeth, materials for temporary restorations or as other materials for prosthetic, conservative and preventive dentistry, as enamel / dentin adhäsvie, Coating material for dental fillings, restorative materials, dentures and natural teeth.
  • Particularly suitable inorganic fillers are amorphous, spherical particles of silicon dioxide and up to 20 mol% of an oxide of at least one element of groups I, II, III and IV of the periodic table. These preferably have a refractive index of 1.50 to 1.58 and an average primary particle size of 0.1 to 1.0 microns.
  • Preferred fillers are also quartz, glass ceramic or glass powder or mixtures thereof. These are preferably Also, a refractive index of 1.50 to 1.58 and an average particle size of 0.4 to 5.0 microns.
  • filler mixtures which contain at least two mutually different fillers.
  • filler mixtures which contain as the first filler component at least one filler based on the above spherical silica particles and as the second filler component at least one quartz, glass ceramic and / or glass powder.
  • the amorphous spherical particles of silica are an amorphous silica-based spherical material which also contains an oxide of at least one metal of Groups I, II, III and IV of the Periodic Table. Strontium and / or zirconium oxide is preferably used.
  • the average primary particle size is in the range of 0.1 to 1.0 .mu.m, in particular 0.15 to 0.5 microns.
  • the refractive index of this inorganic filler is preferably between 1.50 and 1.58, in particular between 1.52 and 1.56. A particularly preferred value is 1.53 ⁇ 0.01. It is also possible to use mixtures of different particles. Fillers of this type are in the DE-PS 32 47 800 described.
  • the filler particles may also be sintered as a mixture of agglomerates having an average particle size of 1 to 30 ⁇ m.
  • fillers are quartz, glass-ceramic and in particular glass powder.
  • the average particle size of this inorganic filler should be between 0.5 and 5.0 .mu.m, in particular between 1.0 and 2.0 .mu.m and particularly preferably between 1.0 and 1.5 .mu.m, while the refractive index values between 1.50 and 1.58, in particular between 1.52 and 1.56 should have. It is also possible to use filler mixtures.
  • Ba silicate glasses having an average particle size in the range from 1.1 to 1.3 ⁇ m, and also Sr silicate glasses having a mean particle size in the range from 1.1 to 1.3 ⁇ m, and also Li / Al silicate glasses having a particle size of 1.1 to 1.3 ⁇ m average particle size of 1.0 to 1.6 microns used.
  • Such powders can be passed through, for example Fine grinding with a RS Ultrafeinstmühle the company Reimbold & dash, Cologne, received.
  • fillers can be used to achieve increased X-ray opacity, the average primary particle size of which should not exceed 5.0 ⁇ m.
  • Such fillers are eg in the DE-OS 35 02 594 described.
  • a further preferred filler used is ytterbium trifluoride.
  • small amounts of microfine, pyrogenic or wet precipitated silica can be incorporated into the dental material to adjust the viscosity, but preferably at most 5 wt .-%, based on the dental material.
  • the total amount of filler consisting of the above-mentioned fillers in the dental material according to the invention is between 0 and 90% by weight, preferably 2 to 85% by weight and more preferably 10 to 80% by weight, depending on the intended use.
  • the proportion by weight of the first filler component is 5 - 60%, in particular 10 - 30%, the proportion of the second filler component 15-85%, in particular 30-70%, in each case based on the total dental material.
  • the inorganic fillers are preferably silanized.
  • adhesion promoter is suitable, for example ⁇ -methacryloxypropyltrimethoxysilane.
  • the amount of adhesion promoter used depends on the type and BET surface area of the filler.
  • Suitable polymerisable organic binders are all binders which are suitable for a dental material, in particular monofunctional or polyfunctional (meth) acrylates or (meth) acrylamides, which can be used alone or in mixtures.
  • these compounds include methyl methacrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, isobutyl (meth) acrylate, cyclohexyl (meth) acrylate, glycerol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, Triethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, ethylene glycol di (meth) acrylate, butanediol di (meth) acrylate, butanediol di (meth) acrylate, hexanediol di (meth) acrylate, decanediol di (me
  • Examples are the reaction products of 1 mole of hexamethylene diisocyanate with 2 moles of 2-hydroxyethylene methacrylate, 1 mole of tri (6-isocyanatohexyl) biuret with 3 moles of 2-hydroxyethyl methacrylate and 1 mole of 2,2,4-trimethylhexamethylene diisocyanate with 2 moles of 2-hydroxyethyl methacrylate, hereinafter referred to as urethane dimethacrylates.
  • N-mono or N-disubstituted acrylamides e.g. N-ethylacrylamide, N, N-dimethylacrylamide, N- (2-hydroxyethyl) acrylamide or N-methyl-N- (2-hydroxyethyl) acrylamide, and N-monosubstituted methacrylamides, e.g. N-ethylmethacrylamide or N- (2-hydroxyethyl) methacrylamide and also N-vinylpyrrolidone and allyl ether.
  • These monomers are liquid at room temperature and are therefore also suitable as a diluent monomer.
  • Suitable crosslinking monomers are monomers having two or more radically polymerizable groups, in particular crosslinking pyrrolidones, such as e.g. 1,6-bis (3-vinyl-2-pyrrolidonyl) hexane, or commercially available bisacrylamides such as methylene or ethylenebisacrylamide, bis (meth) acrylamides, e.g.
  • crosslinking pyrrolidones such as e.g. 1,6-bis (3-vinyl-2-pyrrolidonyl) hexane
  • bisacrylamides such as methylene or ethylenebisacrylamide, bis (meth) acrylamides, e.g.
  • the dental materials according to the invention preferably contain at least one crosslinking monomer.
  • the proportion of crosslinking monomers in the dental material preferably moves between 10 and 95 wt .-%, preferably 20 to 75 wt .-%.
  • the dental materials of the invention may also contain a radically polymerizable, acid group-containing monomer.
  • Acid group-containing monomers are also referred to below as acidic monomers.
  • the dental materials preferably contain a mixture of acidic and non-acidic monomers.
  • Preferred acid groups are carboxylic acid groups, phosphonic acid groups, phosphate groups and / or sulfonic acid groups, which groups may be in the acid form or in the form of an ester. Preference is given to monomers having phosphonic acid groups or phosphate groups.
  • the monomers may have one or more acidic groups, preferred are compounds having 1 to 2 acidic groups.
  • Preferred polymerizable carboxylic acids are maleic acid, acrylic acid, methacrylic acid, 2- (hydroxymethyl) acrylic acid, 4- (meth) acryloyloxyethyltrimellitic acid and the corresponding anhydride, 10-methacryloyloxydecylmalonic acid, N- (2-hydroxy-3-methacryloyloxypropyl) -N-phenylglycine and vinylbenzoic.
  • Preferred phosphonic acid monomers are vinylphosphonic acid, 4-vinylphenylphosphonic acid, 4-vinylbenzylphosphonic acid, 2-methacryloyloxyethylphosphonic acid, 2-methacrylamidoethylphosphonic acid, 4-methacrylamido-4-methylpentylphosphonic acid 2- [4- (dihydroxyphosphoryl) -2-oxa-butyl] -acrylic acid and 2- [2-dihydroxyphosphoryl) -ethoxymethyl] -acrylic acid-2,4,6-trimethyl-phenylester.
  • Preferred acidic polymerizable phosphoric acid esters are 2-methacryloyloxypropylmono- and dihydrogenphosphate, 2-methacryloyloxyethylmono- and dihydrogenphosphate, 2-methacryloyloxyethylphenylhydrogenphosphate, dipentaerythritolpentamethacryloyloxyphosphate, 10-methacryloyloxydecyldihydrogenphosphate, dipentaerythritolpentamethacryloyloxyphosphate, phosphoric mono (1-acryloyl-piperidine-4-) yl) ester, 6- (methacrylamido) hexyl dihydrogen phosphate and 1,3-bis (N-acryloyl-N-propylamino) -propan-2-yl dihydrogen phosphate.
  • Preferred polymerizable sulfonic acids are vinylsulfonic acid, 4-vinylphenylsulfonic acid or 3- (methacrylamido) -propylsulfonic acid.
  • the proportion of acidic monomers in the dental material is between 0 and 85 wt .-%, preferably 0 to 60 wt .-%.
  • the dental materials of the invention may also contain solvents, preferably 0 to 80 wt .-%, particularly preferably 0 to 60 wt .-% and most preferably 0 to 40 wt .-% solvent.
  • Solvents are mainly used in adhesives and coating materials.
  • Preferred solvents are water, methanol, ethanol, phenoxyethanol, isopropanol, ethyl acetate, acetone and mixtures thereof.
  • the dental material can be hot, cold or polymerizable by light.
  • the known peroxides such as dibenzoyl peroxide, dilauroyl peroxide, tert-butyl peroctoate or tert-butyl perbenzoate can be used, but also ⁇ , ⁇ '-azo-bis (isobutyroethylester), benzopinacol and 2,2'-dimethylbenzopinacol are suitable.
  • benzophenone and its derivatives as well as benzoin and its derivatives can be used.
  • Further preferred photosensitizers are the ⁇ -diketones such as 9,10-phenanthrenequinone, diacetyl, furil, anisil, 4,4'-dichlorobenzil and 4,4'-dialkoxybenzil.
  • Camphorquinone is particularly preferred.
  • the use of the photosensitizers together with a reducing agent is preferred.
  • reducing agents are amines such as cyanoethylmethylaniline, dimethylaminoethyl methacrylate, triethylamine, triethanolamine, N, N-dimethylaniline, N-methyldiphenylamine, N, N-dimethyl-sym-xylidine and N, N-3,5-tetramethylaniline and 4-dimethylaminobenzoic acid ethyl ester.
  • photoinitiators of the product group of the acylphosphine oxides, bisacylphosphine oxides or also acyl germanium compounds can be used.
  • radical-providing systems e.g. Benzoyl or lauroyl peroxide together with amines such as N, N-dimethyl-sym-xylidine or N, N-dimethyl-p-toluidine used.
  • Dual-cure systems can also be used for initiation, e.g. Photoinitiators with amines and peroxides. Suitable photoinitiators also include mixtures of UV-light-curing initiators curing in the visible light range.
  • the amount of these initiators in the dental material is usually between 0.01 to 5 wt .-%, preferably 1 to 3.5 wt .-%.
  • the dental material may further finely particulate splinter or bead polymers are incorporated, which may be homopolymers or copolymers of vinyl compounds already described. These homo- or copolymers may in turn be filled with the inorganic fillers described, including radiopaque. Furthermore, the dental material may contain the usual pigmenting agents and stabilizers.
  • the dental materials according to the invention are suitable, for example, for preventing tooth damage caused by Streptococcus mutans and / or lactobacilli or also for preventing prosthesis intolerances caused by Candida albicans .
  • Example 1a Antimicrobial enamel / dentine adhesive for the totaletch technique
  • the antimicrobial agent was replaced with the appropriate amount of GDMA.
  • bovine teeth cast in resin (Bühler Castolite-Resin) were used.
  • the cast-in cattle tooth was roughly ground with P500 grade abrasive paper to dentin or enamel. After a brief finish with P1000 grade abrasive paper and thorough washing with water, the tooth was prepared for test specimen preparation.
  • Phosphoric acid etching gel (enamel preparation GS, Ivoclar Vivadent AG) was applied to the dentin or enamel surface and washed off with water after a contact time of 30 seconds. The thus conditioned surface was lightly dabbed with a paper towel and then applied the adhesive formulation. After an exposure time of 10 seconds, the adhesive layer was polymerized by irradiation with a polymerization lamp (Astralis® 7) for 20 seconds.
  • the tooth prepared in this way was clamped in a shear adhesive mold, a filling composite was applied by means of a round Delrin mold of 4 mm diameter in two layers (a maximum of 3 mm) and in each case for 40 seconds with a polymerization lamp (Astralis® 7 from Ivoclar Vivadent AG,> 500 mW / cm 2 ).
  • the test specimen thus produced was demolded and immediately placed in water. After storage of the specimens at 37 ° C and 24 hours, the shear bond strength was measured with a universal testing machine (Zwick Z010) and a tester device (guillotine) at a speed of 0.8 mm / min. determined. The achieved adhesion values are listed in Table 1.
  • Example 1b Self-etching, antimicrobial enamel / dentine adhesive
  • the antimicrobial agent was replaced with the appropriate amount of UDMA.
  • System.cem is a two-component luting cement for the temporary attachment of zinc oxide-polycarboxylate-based temporary crowns and bridges.
  • the base paste consists of a mixture of zinc oxide, glycerine and water
  • the cat paste consists of a mixture of SiO2 particles, polyacrylic acid, water and olive oil.
  • System.link is a dual-curing, two-component luting cement for the temporary fixation of composite temporary crowns and bridges.
  • the base paste consists of a mixture of SiO 2 particles, a splinter polymer, a monomer mixture and a tertiary aromatic amine.
  • the cat paste consists of a mixture of SiO 2 particles, a splinter polymer, a monomer mixture, dibenzoyl peroxide and a camphorquinone / amine photoinitiator system.
  • Fermit is a temporary one-component filling material that can be cured with blue light.
  • the composition consists of a mixture of SiO 2 particles, a splinter polymer, a monomer mixture and a camphorquinone / amine photoinitiator system.
  • the coating material After exposure for 20 s with a dental polymerization lamp (Bluephase®, Ivoclar Vivadent AG), the coating material cured completely without oxygen inhibition.
  • a dental polymerization lamp Bluephase®, Ivoclar Vivadent AG
  • a composite filling material was prepared having the following composition: component Wt .-% Binder 1) 08.16% Filler 2) 48.5% prepolymer 34% Additives, catalysts and stabilizers 0.7% pigments ⁇ 0.1% 1) Bis-GMA, urethane dimethacrylate, ethoxylated bis-EMA 2) barium glass filler, ytterbium trifluoride, mixed oxide
  • the antimicrobial agent of the formula (I) Into the composite filling material, 3.0% by weight and 5.0% by weight, respectively, of the antimicrobial agent of the formula (I) were incorporated. After exposure for 20 s with a dental polymerization lamp (Bluephase®, Ivoclar Vivadent AG), the depth of cure was determined. As a comparison, the antimicrobial agents triclosan and chlorhexidine diacetate were incorporated in the composite material in an amount of 3.0% by weight and 5.0% by weight, respectively, and the depth of cure was determined (for results, see Table 5).

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  • Health & Medical Sciences (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
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  • Inorganic Chemistry (AREA)
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Claims (14)

  1. Matériau dentaire polymérisable, caractérisé en ce qu'il contient de 0,1 à 3,0 % en poids d'un agent antimicrobien de formule générale (I) :
    Figure imgb0004
     dans laquelle A- représente un ion Cl-, Br-, I- ou F-.
  2. Matériau dentaire conforme à la revendication 1, qui contient de 0,1 à 1,5 % en poids, et de préférence de 0,1 à 0,6 % en poids, de l'agent de formule (I).
  3. Matériau dentaire conforme à l'une des revendications précédentes, qui contient en outre au moins un monomère polymérisable à insaturation éthylénique, en tant que liant, et un amorceur de polymérisation radicalaire.
  4. Matériau dentaire conforme à l'une des revendications précédentes, qui contient en outre une charge organique et/ou inorganique ou un mélange de charges.
  5. Matériau dentaire conforme à la revendication 3, qui contient comme liant au moins un (méth)acrylate ou (méth)acrylamide, monofonctionnel ou polyfonctionnel, ou un mélange de tels composés.
  6. Matériau dentaire conforme à la revendication 3 ou 5, qui contient comme liant un mélange de monomères acides et non acides.
  7. Matériau dentaire conforme à l'une des revendications précédentes, qui contient en outre un solvant, de préférence de l'eau, du méthanol, de l'éthanol, du phénoxy-éthanol, de l'isopropanol, de l'acétate d'éthyle, de l'acétone, ou un mélange de deux de ces solvants ou plus.
  8. Matériau dentaire conforme à l'une des revendications 1 à 3, 5 et 6, qui contient
    - de 0,1 à 1,5 % en poids, et de préférence de 0,1 à 0,6 % en poids, d'agent de formule (I),
    - de 20 à 95 % en poids, de préférence de 30 à 90 % en poids, et mieux encore de 35 à 80 % en poids de liant ;
    - de 0,1 à 5 % en poids, de préférence de 0,3 à 4,0 % en poids, et mieux encore de 0,5 à 3,5 % en poids d'amorceur;
    et en option,
    - de 0 à 90 % en poids, de préférence de 2 à 85 % en poids, et mieux encore de 10 à 80 % en poids de charge;
    et en option,
    - de 0 à 80 % en poids, de préférence de 0 à 60 % en poids, et mieux encore de 0 à 40 % en poids de solvant.
  9. Matériau dentaire conforme à l'une des revendications précédentes, pour utilisation en tant que matériau de plombage, ciment dentaire, matériau de scellement ou matériau de pansement temporaire.
  10. Matériau dentaire conforme à l'une des revendications 1 à 8, pour utilisation en tant qu'adhésif dentinaire en masse fondue.
  11. Matériau dentaire conforme à l'une des revendications 1 à 8, pour utilisation en tant que matériau de revêtement pour plombages, matériaux de restauration, prothèses dentaires et dents naturelles.
  12. Matériau dentaire conforme à l'une des revendications 1 à 8, pour empêcher les dommages dentaires provoqués par Streptococcus mutans et/ou les lactobacilles.
  13. Matériau dentaire conforme à l'une des revendications 1 à 8, pour empêcher les irritations dues au port d'une prothèse et provoquées par Candida albicans.
  14. Utilisation d'un agent de formule (I) pour la préparation d'un matériau dentaire polymérisable conforme à la revendication 1.
EP10162250.4A 2010-05-07 2010-05-07 Matières dentaires antimicrobiennes Active EP2384733B1 (fr)

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EP10162250.4A EP2384733B1 (fr) 2010-05-07 2010-05-07 Matières dentaires antimicrobiennes
JP2011096597A JP2011236211A (ja) 2010-05-07 2011-04-22 抗菌歯科材料
US13/097,100 US20110275675A1 (en) 2010-05-07 2011-04-29 Antimicrobial Dental Materials

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EP3412273B1 (fr) 2016-02-01 2021-06-16 FUJIFILM Corporation Matiériau de dévitalisation dentaire et kit de dévitalisation dentaire

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